You’re right. This whole process seems to involve a great deal of trying to smash existing conceptions, rather than just learning a system. When I learned D&D, even though it was my first tabletop RPG, I still had this problem, but it was in bringing in expectations from video games. Now, rather than video games, it’s D&D influencing me.
Pretty much every time I give an obstacle, I look at the list of what the OBs mean, and go from there (like the OB 6, in my example above. It was referred to as “ludicrously difficult,” and I thought, “That sounds right.”)
This is one of the things that made me fall in love with BW, pretty much as soon as I found it. In D&D, we’re always scrambling for success - no matter what, we HAVE to succeed at everything we do. Failure hurts. BW failure doesn’t hurt nearly so bad - in D&D, it’s usually regarded as a complete, unmitigated failure, whereas in BW, failure can be a lot of fun.
This last game, I had a player argue with me about an OB - he was saying it was too easy! He was telling me about how his character should, because of X, Y, and Z reasons, have absolutely no chance of succeeding, but she’s going to try her damnedest anyway, because that’s who she is.
I just had to pause and marvel at the guy, who I’ve known and gamed with for years. When it came to important things, he always had to succeed. And now? Now he was embracing failure. It was beautiful.